Manufacture of acid dyestuffs of the phenonaphthosafranine series



, Patented sept l, l g Q i r UNITED STATES PATENT OFFICE.

PA L LAEUGER, or BASEL, SWITZERLAND, ass enoa TO THE FIRM or J. a GEIGY,

' s. A., ornAsnnswrrznanaun. y ,1

MANUFACTURE or non) nYEsrUFrsorrHn PHENONAPH'IHOSAFRANINE SERIES.

No Drawing, Original application filed February 4, 1927, Seria1 No.166,021, and in Germany February v is, 192 Divided and this applicationfiled December 28,1927. Serial No. .'243,21'o.

This application is divisional, of applicaposition to the amino-groupaccording to the 10 tion Sen. No.166021 filed February 4,1927. formula:i y I According to the present invention, reddish z NH, blue to blueacid dyestuffs of the phenonapln o 5 thosafranine series which, whendyed, are fast to alkali, very fast to light and for the greati l estpart'have good equalizing properties, are with anisorosindulinesulphonie acid of the obtained by condensing'a'para-amino-phenol general formula:

derivative having a sulpho-group in ortho 011 SOaH i 15 having at leasttwo sulpho groups, one of and Y a univalent radical, such as sulpho,

, them being in position 6, the other in one of halogen, alkyl, alkoXy,acidylamino, eto, 20 the positions 1 andj2 and the. third, if it beNVllllSli R and R stand for hydrogen, alkyl present, in any position,whereby in the above and aryll v y i 1 formulae Z represents hydrogen,alkyl,:alkoxy The reaction takes plaeesaceording to the and halogen, Xan acid radical, such as SO H, following formula:

15 11 14 -12 e v r {V a 1 30 The resulting phenonaphthosaphranine-sul-(16)' pOS:lt-lO1 1: O f one sulpho-group tothe nhonic acids arecharacterized by the ortho safranine-nitrogen, whichvhasthe effect inlyoiving tothis l-6lsulplio groupthe dyestuffs are fast to alkali.

The dyestuffs obtained according to this process are soluble-in waterand in sulphuricacid.

' This process of manufacture could notbe. foreseen, since no similarkind of condensation withortho-aininoarylsulphonicacids has beendiscovered and the known hindering effeet upon the reactions possessedby strong acid radicals in ortho-positionto the aminogroup did notallow'ofaprospect of success. Whilst derivatives of-para-phenylene-diamine yield blue to blue-greendyestutfs of outstandingiclearness'of tint and pronounced fastness especially to alkali andlight, it is to be noted that with the correspondin derivatives ofpara-amino-phenols redder-blue tints of similar properties are obtained.

The isorosinduline-(i-sulphonic acidsused as parent materials canbe madefrom-the sulplionic' acids of the neutral blue series by treatment withsulphites in accordance with U.' S. patent specification No. 617,703 andsubsequent oxidation. Positions 4: and 8 to may contain alkyl-,alkyloxy, hydroxy The following example illustrates the in vention,-theparts being by weight, I

This enample relates to the manufacture ofthe dyestufi of the formula:

SOSH

N: do 7 V N N CzH:

O/ l oan \smH O ture'thereof is the isorosindiilinedisulphonic acidobtained by converting the isorosi nduline-l-sulphonic acid, which maybe obtained tatc. ,The beautifully crystalline dyestulf carboxyoracidylamino-groups and halogen.

The parent material used for the \maniifacseparates on salti ng out; itdissolves to a green solution in sulphuric acid and dyes wool reddishblue tints. In addition to good equalizing power this dyestiifi':exhibits im- 1 A process for the manufacture of'eqiial- *izing aciddyestuffs of the plienonaplitliosafranineseries fastto alkali,consisting incondensing a para-anrinophen0l derivative h av ingasulpho-group in ortho position to the amino-group according to thegeneration i KI ' on/ soar mula:

with anisorosindiiline sulphonic acid with at least two sulpho-groupsaccording to the general formula where R and R represent hydrogen alkylor LIyl, Wl'1llSl3 Z represents hydrogen, alkyl, al-

koxy and halogen, X an acid radical and 7X alunivalent radical.

-2. As a new article of manufacture, the herein described dyestuflf ofthe phenonaphthosafranine series oftlie constitution:

constituting a crystalline body dissolving to I s oin a green solutionin sulphuric acid and dyeing wool reddisli blue tints of good e ualizingpowpr and improved fastness to light and alk a i.

In witness whereof I have hereunto signed my name this 15th day ofDecember 1927.

, ileULL EU

